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Method for synthesizing tetrahydrocarbazoles compound

A technology of tetrahydrocarbazoles and synthetic methods, which is applied in the field of fine chemicals, can solve problems such as harsh operating environment and environmental pollution, and achieve the effects of environmental friendliness, reduced production costs, and mild reaction conditions

Inactive Publication Date: 2011-11-23
NANTONG HAIDI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since then, the synthesis of 1,2,3,4-tetrahydrocarbazole mainly uses acetic acid as a solvent and catalyst, but the use of acetic acid in industry has harsh operating conditions and serious environmental pollution

Method used

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  • Method for synthesizing tetrahydrocarbazoles compound
  • Method for synthesizing tetrahydrocarbazoles compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 104g (0.68mol) of phenylhydrazine hydrochloride (95% content), 400g of water and 45g of 30% hydrochloric acid into a 1000ml four-necked bottle, raise the temperature to 40°C under stirring and start to add 70g (0.714mol) of cyclohexanone dropwise, then As the dropwise addition proceeds, the reaction temperature rises slowly, and the temperature control does not exceed 55°C, and the dropwise addition is completed in about 1.5 hours. Then keep warm at 55-60°C for 1 hour, cool to below 30°C, filter, wash the filter cake until neutral, and dry to obtain 114.5g of tetrahydrocarbazole with an HPLC content of 99.1%.

Embodiment 2

[0024] Add 112g (0.68mol) of phenylhydrazine hydrochloride (88% content), 400g of water and 45g of 30% hydrochloric acid into a 1000ml four-necked bottle, raise the temperature to 40°C while stirring and start to add 70g (0.714mol) of cyclohexanone dropwise, then As the dropwise addition proceeds, the reaction temperature rises slowly, and the temperature control does not exceed 55°C, and the dropwise addition is completed in about 1.5 hours. Then keep warm at 55-60°C for 1 hour, cool to below 30°C, filter, wash the filter cake until neutral, and dry to obtain 112g of tetrahydrocarbazole with an HPLC content of 98.2%.

Embodiment 3

[0026] Add 74.3g (0.68mol) of phenylhydrazine (99% content), 400g of water and 160g of 10% sulfuric acid into a 1000ml four-necked bottle, and raise the temperature to 40°C while stirring and start to add 70g (0.714mol) of cyclohexanone dropwise. The reaction temperature rises slowly during the addition, and the temperature control does not exceed 55°C, and the dropwise addition is completed in about 1.5 hours. Then keep warm at 55-60°C for 1 hour, cool to below 30°C, filter, wash the filter cake until neutral, and dry to obtain 110.2g of tetrahydrocarbazole with an HPLC content of 98.6%.

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Abstract

The invention discloses a method for synthesizing a tetrahydrocarbazoles compound. The method is a green preparation method for synthesizing the tetrahydrocarbazoles compound by using phenylhydrazine hydrochloride or phenylhydrazine and cyclohexanone as raw materials and synthesizing 1,2,3,4-tetrahydrocarbazole in one step through condensation and ring-closing. The method provided by the invention comprises the following steps of: mixing the phenylhydrazine hydrochloride or phenylhydrazine, water and inorganic acid; dripping the cyclohexanone at the temperature in a range of 40-90 DEG C for 0.5-4 hours; and after dripping the cyclohexanone, keeping the heat for 0.5-3.0 hours to obtain the high-content 1,2,3,4-tetrahydrocarbazole. The method for synthesizing the 1,2,3,4-tetrahydrocarbazole is economical, simple and convenient and has the advantages of moderate reaction conditions, high yield and product purity, environmental friendliness and the like.

Description

technical field [0001] The invention relates to a method for synthesizing tetrahydrocarbazole compounds, belonging to the field of fine chemicals. Background technique [0002] Carbazole compounds are an important class of fine chemical intermediates, widely used in the fields of dyes, pigments, medicines and pesticides, especially for the preparation of high-grade organic pigments. In recent years, the research and application of carbazole and its derivatives are being further deepened, and the demand for carbazole is also increasing. Carbazole is mainly derived from coal tar, but its separation and refining process is complex, energy consumption is high, product purity is low, and the output is limited, which cannot meet market demand. The chemical synthesis of carbazole has attracted the interest of researchers. There are many methods in the literature on the synthesis of carbazole. The Borsche method for synthesizing carbazole is one of the most industrialized methods. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86
Inventor 倪海平侯启军
Owner NANTONG HAIDI CHEM
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